Bleeding Gums learned his musical skills at the feet of Blind Willie Witherspoon. When Bleeding Gums was ready to launch his musical career, Willie wanted to give Bleeding Gums his saxophone: "I've been playing jazz for thirty years and I just can't make a go of it." Bleeding Gums told him it that it wasn't a saxophone, but an umbrella, which meant that Willie had actually been playing an umbrella for some thirty years. When Wilie asked why no one had told him, Bleeding Gums explained that no one had informed him of the mistake because "We all thought it was funny."

Blind Willie Witherspoon may be a reference to blues musician Blind Willie McTell. McTell enjoyed a long and prolific recording career but never had a major hit record, similar to Witherspoon's saying "I just can't make a go of it" after thirty years of playing jazz.